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Entourage: The 20 Best Cameos

Stephen Carty

12 Sep 2011 09:00Last updated: 9 Oct 2015 07:32

The eighth and final season of Entourage is drawing to a starry close, like Vinnie Chase doing one last lap of the LA talent-pool. It's time to celebrate by paying tribute to some of the show’s most satisfying cameo appearances. Of course, there’s more to HBO’s contagious bromance than celebrities playing twisted versions of themselves – it’s all about friendship, kids – but they’ve always been fun, spot-on and added another layer of realism to the already pitch-perfect depiction of Hollywood life life. Come'on, where else would you see Sydney Pollack and Kanye West on the same cast list? Here's our pick of 20 favourites.

Gary Busey has always had an unpredictable presence, but here his full eccentricity is unleashed. Playing himself (surely the role of a lifetime) as an intimidating actor-turned-artist, Busey's unsettling intensity and toothy tough-guy vibe intimidates the gang after they visit his exhibition. Clearly, some of his pseudo-philosophical ramblings were improvised (see the true expression of surprise on Jerry Ferrara's face after being 'cleansed'), while at times you wonder if he's even acting.

Memorable Quote: Busey analysing Ari: “You are a gut maggot… with no guts.”

Appears in: New York (Season 1, Episode 8)

Given that he's been playing an exaggerated version of himself on Curb Your Enthusiasm for years, Larry David was a natural fit for Entourage. Appearing as one of Ari's clients, Larry launches into one of his trademark fast-talking tirades after learning that his agent ditched him to go to a Lakers game with Vin Diesel. Going on to recognise Drama before unintentionally disapproving of his goatee, the awkwardness and bemused facial expressions are vintage Curb.

Memorable Quote: Larry, mid-babble: “What language are you talking? Is this an excuse? I don't know what you're talking about. What happened? I still don’t know, you’re talking Chinese.”

Appears in: Aquamansion (Season 2, Episode 3)

A perfect example of how naturally the cameos slot into the show, Ralph Macchio is exactly the type of actor you imagine Johnny Drama hanging about with back in his heyday. With a trip to the Playboy mansion coming up, Drama attempts to get his ban revoked by asking family man Macchio to own up and take the fall as the real guilty party. But under the settled-down facade, the former Karate Kid still lives for Cuervo-fuelled nights at Hugh Hefner's. Of course, the Hef also pops up (giving an also-cameoing Pauly Shore a lifetime ban), but this one's all about Daniel San.

Memorable Quote: Ralph to Drama: “You know when it comes to the mansion it’s every man for himself.”

Popping up three times in the last two seasons, Bob Saget is now more a recurring player than throwaway cameo. Doing everything he can to dispel his family-friendly Full House image, Saget first arrived as a bong-smoking, robe-clad, sex-obsessed neighbour of Vinnie's who likes to hang out with high-class prostitutes. Since then he's nicked jobs from Drama, sniffed out that E was contemplating anal sex and bargained to have his end away in a top agent's office. We can only hope he’s just a little bit like this in real life.

How the hell did Doug Ellin and co. pull this one off? Okay, so Entourage has had plenty of big-name talent pop up over the years, but James frickin' Cameron? In the 12 years between Titanic and Avatar Jim’s largely been off the Hollywood radar, yet he found time for HBO's tinsel-town dramedy. As such, we're very grateful, with J-Cam stepping in to direct Vinnie as Aquaman. Because hey, if anyone's perfect for a water-based superhero picture, it's Jim.

Memorable Quote:Jim to Vince at the premiere of Aquaman: “Okay, don’t party too late tonight. If they don’t like the movie, the reshoot’s 8:00am tomorrow. Okay?”

Appears in: The Abyss (Season 2, Episode 14)

A very brief one this, but worth mentioning nonetheless. Appearing when Ari is desperately trying to persuade all his clients to come with him to a new splinter agency (using a Coffee Bean to host meetings), this Richard Schiff wants to be put in movies. And not just any movies, but tough-guy Scorsese pictures where he gets to swear and intimidate. With the simmering undercurrent of rage and a quiet intelligence there’s shades of Toby Ziegler, but with an added baseball cap and the desire to use swear words on the big screen.

Jimmy Woods’ storyline for the season three opener might seem unimportant – two of his premiere tickets for Aquaman are given to the gang – but he dominates the episode anyway. Bursting in to Ari’s rundown temporary agency as a hairtrigger-temper ball-breaker (“Fucking elevator’s broken Lloyd, are you aware of that?”), it’s James Woods as you imagine James Woods to be: shades, explosive swearing and a hot blond on his arm. The highlight? Where he stomps round to the boys’ mansion to intimidate Drama and Turtle into giving his tickets back via visual intercom (“Holy shit, it’s Woods!”). There aren’t many better Entourage cameos.

Turning up sporadically since season three, Seth Green became something of a nemesis for Eric. First appearing when E just began seeing Sloan (the immaculate Emmanuelle Chriqui), he started off as seemingly-friendly acquaintance before swiftly snowballing into a passive aggressive irritant who hides insults behind false pleasantries. No matter how much you love Seth in Buffy, the Austin Powers series or Family Guy, here you’ll want to join Drama in giving him a swift punch to the chops.

Though only book-ending the episode with brief screen time, the mercurial writer-director informs an entire instalment of Ari's antics. Arranging to meet in person so he can hand in his latest script (since he doesn't trust messengers), Shyamalan then tasks the mouthy super-agent with reading the whole thing that night, as there will be a quiz the next morning. After an evening which includes Ari rudely rushing through dinner with Mrs Ari's friends, a trunk full of sex toys and a some jail time, he somehow manages to read the screenplay. Only to be told Night has changed the whole thing and wants him to re-read it. From the top, so he can get the flow.

Memorable Quote: Ari: "We're in a cemetery at night, even for you this is bizarre."Night: "Don't be an ass, I'm shooting an AMEX commercial."

Another one who pops up from time to time, Jeffrey Tambor is Ari's longtime client and – as he'd prefer to be thought of – his close friend. Whether it's while Ari’s having marital problems, trying to make a life-changing career decision or playing in a charity golf outing, Jeff’s always there for his fast-talking, power-walking agent. Bored, insecure and caring to a fault, this meta Tambor is the perfect yin to Ari Gold’s busy, cocky and abrasive yang. We’d love it if he called us each day for lunch.

Memorable Quote: Jeffrey, reassuring Ari: “I am no stranger to scandal, there was that little incident on Arrested Development. You haven’t heard about it, there’s no reason to hear about it.”

Appears in: Pie (Season 5, Episode 9)

With Vinnie's career dangling by a thread, he manages to snag the second lead in fire-fighting action-drama Smoke Jumpers. However, when it turns out that star Jason Patric is an intimidatingly-serious and overly-competitive diva who blatantly nicks all his lines, things don't look so good. We should be concerned for VInce here, but Patric is such an intense delight ("One take? LOVE THAT!"), spending his trailer-time practicing punches, doing crunches or chugging protein shakes. One thing though: don't steal his chair.

Memorable Quote: Drama, offering advice to Vinnie: "Remind him that he got molested in Sleepers. That'll throw him off balance."

Appears in:Return To Queen Blvd (Season 5, Episode 12)

Doug Ellin and his team have admitted that it was tough to get cameos in the early days, but the appearance of Martin Scorsese in season five proves that by then, nobody was untouchable. Despite Eric's best efforts to convince an also cameoing Gus Van Sant into hiring Vince, it was Marty (spoiler alert) who provided the career defibrillation with his olive branch offer for Chase Jr to star in his adaptation of The Great Gatsby. After a darker than usual season, this was a satisfying punch-the-air moment of triumph that we all cheered for.

Though when we first met Turtle he was quite happy to mooch off Vinnie's fast-rising fame, season six saw him develop a need to be his own man. Following a what-are-you-doing-with-your-life phone call from his mother, the rap-loving goofball's feelings of being worthless were made worse when both Vince and girlfriend Jamie-Lyn Sigler (played by, surprisingly, Jamie-Lyn Sigler) both bought him expensive cars. Poor guy. Out cruising, a brief run in with Curtis '50 Cent' Webb didn't do anything to make him feel better...

David Schwimmer doesn't so much play an amplified version of his screen-persona as he does a twisted, bizarro twin. Staring at Ari's junior agents with unspoken disgust after they pitch him variations on neurotic, Ross-like characters (despite the fact he’s just told him he wants something fresh), Schwimmer is a cursing, sarcastic joy. Still, it works out well for Ari’s “favourite Friend”, as he takes a meeting with rising agent Lizzie Grant (Autumn Reeser) because A) she has the best idea and B) because he fancies her. And not necessarily in that order.

Like James Cameron, Aaron Sorkin is a talent that you can't really believe gave up his valuable time (writing, tinkering on scripts, generally creating masterpieces) to pop up on telly. But happily, here we are. With Ari's old friend and recent colleague Andrew Klein (Gary Cole) imploding on the back on a work-related affair, his best chance to keep his job is to do the impossible: sign and deliver Sorkin. Though his continual promises seem empty ("I'm right there! He's coming in!"), the West Wing man finally appears at the Miller-Gold agency, just as Andrew's now-estranged wife has hidden his pivotal meeting notes...

Memorable Quote: Sorkin, while Ari is trying to keep a meeting going: “It’s okay, the meeting is over; I’m just flirting with her.”

Appears in: Scared Straight (Season 6, Episode 11)

Another brief one, but like the aforementioned Ralph Macchio, Dean Cain is exactly the level of actor you expect Drama to be coming up against. Despite having found 'fame' and 'success' (What? He was on a billboard!) with Eddie Burns' network hit Five Towns, Drama is once again found singing for his supper at an audition for the new Melrose Place. Though one of the producers (William Fichtner, not playing himself) loves Johnny for the part, the older Chase sibling can't help but meltdown when he realises Cain is also auditioning...

Memorable Quote:"He's testing too? I thought it was just me... (it's) fucking Superman."

Appears in: Give A Little Bit (Season 6, Episode 12)

There have been a few great cameos over the years on Entourage, but Matt Damon is a strong contender for best of the bunch. In the season six finale, Vince is continually cornered (and, arguably, stalked) by Damon, who intimidatingly pressures him into donating big sums of cash to charity, by way of online conferences with Bono (yes, that Bono). Playing himself as a combustible, fund-raising-obsessed psycho on the edge of explosion, he's huge fun, and his post-credits flip-out is legendary clip destined for YouTube fame.

Memorable Quote: Drama, after being strong-armed into putting Vince on the phone: "Sorry, he Jason Bourne'd me!"

Appears in: Bottom's Up (Season 7, Episode 5)

Hey, he's keen for cameos in pretty much every Marvel movie going, so why not Entourage? Introduced via writer-director Randall Wallce (also popping up as himself) as "the man, the myth, the legend", Stan the man meets Vinnie to discuss new superhero project Air-Walker. Though it's just great having the leader of the Merry Marvel Marching Band appear full stop, he also gamely sends himself up, recognising Vince's new porn star girlfriend but not quite able to place her...

Memorable Quote: Stan, to porn star Sasha: “Oh, you look familiar…”

Appears in: Bottom's Up (Season 7, Episode 5)

Forget about his better-known appearances in The Hangover series, the real Mike Tyson cameo came in Entourage. Meeting with Ari to ensure his agent still has the love for him, Tyson is brilliantly self-deprecating, pitching himself for a black Brady Bunch show, and then opportunistically trying to nab Jessica Simpson (who, yes, you guessed it, also stars briefly as herself) as co-star. This one is a little dated already given that there’s discussions about Mike doing The Hangover sequel (“I need more money and I need more talking time”), but it’s genius nonetheless.

Memorable Quote: “What I need really is a steady, respectable job. Something nine to five. I need more structure in my life.”

Appears in:Lose Yourself (Season 7, Episode 10)

The cleverly-titled season seven finale boasted a huge number of fun cameos (including Christina Aguilera), but undoubtedly the best was saved for last. Depressed after splitting from his porn star girlfriend Sasha Grey (playing herself) and with his substance abuse problems spiralling out of control, Vinnie checked into a hotel where he crashed Marshall Mathers' huge party. Getting a bit too rowdy, Vince insulted a few guests and ends up in fisty-cuffs with the infamous badboy rapper, who might not even be aware there's a camera on him, it feels so Slim Shady.

Memorable Quote: Vince to Eminem: "Oh, what? Are you too mainstream now to fight your own fights, Marshall?”